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Rivera was born and raised in New York City and lived most of her life in or near the city. She was born as Ray Rivera and was of Puerto Rican and Venezuelan descent.[1] She was abandoned by her birth father José Rivera early in life and became an orphan after her mother committed suicide when Rivera was three years old.[9] Rivera was then raised by her Venezuelan grandmother, who disapproved of Rivera's effeminate behavior, particularly after Rivera began to wear makeup in fourth grade.[9] As a result, Rivera began living on the streets at the age of eleven and worked as a prostitute. She was taken in by the local community of drag queens, who gave her the name, "Sylvia."[10]

Rivera's activism began during the African-American Civil Rights Movement (1955–68) and continued through the anti-war movement during the Vietnam war (mid-1960s) and second-wave feminist movements (mid-1960's). Rivera stated she was a regular patron of the Stonewall Inn and that she was present during the Stonewall Riots in 1969, when gay men, lesbians, bisexual people, drag queens, street people and trans people rose up against what started as a routine raid by the police.[11] At least one Stonewall historian, David Carter, has questioned Rivera's links with the Stonewall Inn and the protests based on contradictory statements she made as well as testimony relayed to him by early gay rights activists, including Marsha P. Johnson who denied Rivera was present at the riots.[12] Rivera also became involved in Puerto Rican and African American youth activism, particularly with the Young Lords and Black Panthers.[9]

At different times in her life, Rivera battled substance abuse and lived on the streets, largely in the gay homeless community at the Christopher Street docks.[3] Her experiences made her more focused on advocacy for those who, in her view, mainstream society and the assimilationist sectors of the lesbian, gay, bisexual, and transgender (LGBT/queer) communities were leaving behind.[13]

At a 1973 Gay liberation rally in New York City, Rivera, representing STAR, gave a brief speech from the main stage. In it she called out the heterosexual males who were preying on vulnerable members of the community. Rivera espoused what could be seen as a third gender perspective, saying that LGBT prisoners seeking help, "do not write women. They do not write men. They write to STAR."[14] At the same event, Rivera and fellow queen Lee Brewster jumped onstage during feminist activist Jean O'Leary's speech and shouted "You go to bars because of what drag queens did for you, and these bitches tell us to quit being ourselves!"[13][15]

In early July 1992, shortly after the 1992 New York City Pride March, Rivera's close friend Marsha P. Johnson was found dead floating in the Hudson River off the West Village Piers. Police promptly ruled Johnson's death a suicide, despite the presence of a head wound on the body.[16] Johnson's friends and supporters, Rivera included, insisted Johnson had not been suicidal, and a people's postering campaign later declared that Johnson had earlier been harassed near the spot where her body was found. In May 1995, Rivera tried to commit suicide by walking into the Hudson River.[17] That year she also appeared in the Arthur Dong documentary episode "Out Rage '69", part of the PBS series The Question of Equality,[18] and gave an extensive interview to Gay journalist Randy Wicker. In the interview she discusses her suicide attempts, Johnson's life and death, and her advocacy for the poor and working class gays made homeless by the AIDS crisis.[3]

In the last five years of her life Rivera renewed her political activity, giving many speeches about the Stonewall Uprising[19] and the necessity for unity among transgender people - including drag queens and butch dykes - to fight for their historic legacy as people in the forefront of the LGBT movement. She traveled to Italy for the Millennium March in 2000 where she was acclaimed as the 'Mother of all gay people'.[11] In early 2001, after a church service at the MCC of New York referring to the star in the sky that announced the birth of Jesus she decided to resurrect Street Transvestite Action Revolutionaries as an active political organization (now changing "Transvestite" to the more recently coined term, "Transgender," which at that time was understood to include all gender-nonconforming people).[20] STAR fought for the New York City Transgender Rights Bill and for a trans-inclusive New York State Sexual Orientation Non Discrimination Act. Also STAR sponsored street pressures for justice for Amanda Milan, a transgender woman who was murdered in 2000.[11] Rivera also attacked the Human Rights Campaign and the Empire State Pride Agenda as organizations which were standing in the way of transgender rights. On her death bed she met with Matt Foreman and Joe Grabarz of the Empire State Pride Agenda in order to negotiate transgender inclusion in ESPA's political structure and agenda.

Rivera refused to have drag queens and drag culture erased from the newly prominent, assimilationist gay rights agenda, by revisionist and newly-out, self-proclaimed "gay leaders" who were seeking to make the community look more attractive to the heterosexual majority by focusing on military service and marriage equality.[11][21] Rivera's conflicts with these new, assimilationist LGBT groups were emblematic of the new, mainstream LGBT movement's strained relationship to the radical politicos and radical politics of long-term, gay liberation activists who had paved the way for assimilation to even be possible. After her death, Michael Bronski recalled Rivera's anger when she felt that she was being marginalized within the community:

After Gay Liberation Front folded and the more reformist Gay Activists Alliance (GAA) became New York's primary gay rights group, Sylvia Rivera worked hard within their ranks in 1971 to promote a citywide gay rights, anti-discrimination ordinance. But for all of her work, when it came time to make deals, GAA dropped the portions in the civil rights bill that dealt with transvestitism and drag — it just wasn't possible to pass it with such "extreme" elements included. As it turned out, it wasn't possible to pass the bill anyway until 1986. But not only was the language of the bill changed, GAA — which was becoming increasingly more conservative, several of its founders and officers had plans to run for public office — even changed its political agenda to exclude issues of transvestitism and drag. It was also not unusual for Sylvia to be urged to "front" possibly dangerous demonstrations, but when the press showed up, she would be pushed aside by the more middle-class, "straight-appearing" leadership. In 1995, Rivera was still hurt: "When things started getting more mainstream, it was like, 'We don't need you no more'". But, she added, "Hell hath no fury like a drag queen scorned".[22]

According to Bronski, Rivera was banned from New York's Gay & Lesbian Community Center for several years in the mid-nineties, because, on a cold winter's night, she aggressively demanded that the Center take care of poor and homeless queer youth. A short time before her death, Bronski reports that she said:

One of our main goals now is to destroy the Human Rights Campaign, because I'm tired of sitting on the back of the bumper. It's not even the back of the bus anymore — it's the back of the bumper. The bitch on wheels is back.[22]

Rivera's struggles did not relate exclusively to gay and trans people, as they intersected with issues of poverty and discrimination faced by people of color. The transgender person-of-color activist and scholar Jessi Gan discusses how mainstream LGBT groups have routinely dismissed or not paid sufficient attention to Rivera's Latina identity, while Puerto Rican and Latino groups often have not fully acknowledged Rivera's contribution to their struggles for civil rights.[9] Tim Retzloff has discussed this issue with respect to the omission of discussions about race and ethnicity in mainstream U.S. LGBT history, particularly with regard to Rivera's legacy.[23]

Rivera died during the dawn hours of February 19, 2002 at New York's St. Vincent's Hospital, of complications from liver cancer.[2] Activist Riki Wilchins noted, "In many ways, Sylvia was the Rosa Parks of the modern transgender movement, a term that was not even coined until two decades after Stonewall".[24]

An active member of the Metropolitan Community Church of New York, Rivera ministered through the Church's food pantry, which provides food to hungry people. Recalling her life as a child on the streets, she remained a passionate advocate for queer youth, and MCC New York's queer youth shelter is called Sylvia's Place in her honour.[25]

Named in her honor (and established in 2002), the Sylvia Rivera Law Project is dedicated "to guarantee that all people are free to self-determine gender identity and expression, regardless of income or race, and without facing harassment, discrimination or violence".

In 2002, actor/comedian Jade Esteban Estrada portrays Rivera in the well-received solo musical ICONS: The Lesbian and Gay History of the World, Vol. 1(directed by Aliza Washabaugh-Durand and produced by Aliza Washabaugh-Durand and Christopher Durand) winning Rivera renewed national attention.

In 2005, the corner of Christopher and Hudson streets was renamed "Sylvia Rivera Way" in her honour. This intersection is in Greenwich Village, the neighborhood in New York City where Rivera started organizing, and is only two blocks from the Stonewall Inn.[26]

In January 2007, a new musical based upon Rivera's life, Sylvia So Far, premiered in New York at La Mama in a production starring Bianca Leigh as Rivera and Peter Proctor as Marsha P. Johnson. The composer and lyricist is Timothy Mathis (Wallflowers, Our Story Too, The Conjuring), a friend of Rivera's in real life. The show moved off-Broadway in the winter of 2007/2008.

The Spring 2007 issue of CENTRO: Journal of the Center for Puerto Rican Studies, which was dedicated to "Puerto Rican Queer Sexualities" and published at Hunter College, included a special dossier on Sylvia Rivera, including a transcription of a talk by Rivera from 2001 as well as two academic essays exploring the intersections of Rivera's trans and Latina identities.[9][11][23] The articles in this journal issue complement other essays by Puerto Rican scholars who have also emphasized Rivera's pioneering role.[27][28]

In 2014, The Social Justice Hub at The New School's newly opened University Center was named the Baldwin Rivera Boggs Center after activists James Baldwin, Sylvia Rivera, and Grace Lee Boggs.

Rivera's gender identity was complex and varied throughout her life.[3][1] In 1971 she spoke of herself as a "half sister"[31] In her essay "Transvestites: Your Half Sisters and Half Brothers of the Revolution" she specifically claims her use of the word "transvestite" as only applying to the gay community: "Transvestites are homosexual men and women who dress in clothes of the opposite sex."[31]

In interviews and writings in her later years, notably her 1995 interview with Randy Wicker and her 2002 essay, "Queens In Exile, The Forgotten Ones," she expressed a fluid take on gender, referring to herself alternately as a gay man,[4] a "gay girl,"[3] a drag queen/street queen,[1][6][7] and again as a gay man,[1] embodying all of these experiences and seeing none of these identities as excluding the others.[1] She writes of having considered gender reassignment surgery earlier in life, but of ultimately choosing to reject it, only taking hormones near the end of her life.[1]

I left home at age 10 in 1961. I hustled on 42nd Street. The early 60s was not a good time for drag queens, effeminate boys or boys that wore makeup like we did. Back then we were beat up by the police, by everybody. I didn’t really come out as a drag queen until the late 60s. when drag queens were arrested, what degradation there was. I remember the first time I got arrested, I wasn’t even in full drag. I was walking down the street and the cops just snatched me.[32]

People now want to call me a lesbian because I’m with Julia, and I say, “No. I’m just me. I’m not a lesbian.” I’m tired of being labeled. I don’t even like the label transgender. I’m tired of living with labels. I just want to be who I am. I am Sylvia Rivera. Ray Rivera left home at the age of 10 to become Sylvia. And that’s who I am.[1]